Words and photos Michael Halsband

Escorting Hunter S. Thompson on a week-long fact-finding mission to Cuba could be a dream or a nightmare, depending on your threshold for “adventure.”

Perhaps best known for shooting the now-ubiquitous Warhol and Basquiat boxing series, Michael Halsband also served as the official tour photographer for both the Stones and AC/ DC. But when he accepted the assignment to act as cultural liaison and tour guide for the father of Gonzo, Michael didn’t know what he was getting into. Ten years after the trip, he’s still figuring it out.

In the winter of 1999 I was visiting a friend, the then-Editor In Chief of US magazine, when he got a call from Hunter S. Thompson. I heard my friend mention that I was there, and that I knew a lot about Cuba. Then he said, “Maybe you should talk to him,” and put me on the phone. Hunter explained that he was going to Cuba to do a story for Rolling Stone magazine, and asked me almost immediately if I would be interested in going with him. I said, “Uhh…it sounds like fun. Why not?” Later it was very clearly expressed to me by the Managing Editor at Rolling Stone that I was not on assignment, but that I had only been hired to make sure that Hunter got in and out of Cuba safely. I had no obligation to do anything as a photographer. All I was going there to do was babysit.

The idea was for Hunter to be filing every day from Havana, this newslike, day-by-day reporting. I asked him what he was interested in doing while he was down there. He had some idea, but it was very hard for me to follow. It was some kind of conspiracy theory. He was following a line, a thread of a thought, but I wasn’t really getting it. “That’s what I’m interested in, and I’m not going to give you all the pieces,” is what he told me.

Hunter S. Thompson in Cuba

Hunter flew from Colorado, I flew from New York, and we met in Mexico. I had read most of Fear and Loathing in Las Vegas on my way to Mexico and finished the rest of it on the plane to Havana. I didn’t really know what his other books were like, but when I met him I was thinking, “Alright, at least he’s done one masterpiece. I don’t know what he’s done since then, but this is an amazing piece of literature.” He was able to write something in complete stream of consciousness and have it come across so well. That’s have it flow through us so clearly.

After we checked into our rooms in Havana we started talking. He had a plan for the trip, and I was trying to hold off on that plan for a day or two and just let things happen, but I think he was very desperate to keep his flow—having activities in place and filing every day. I told him, “You know, this could be an amazing opportunity for a real shift in your work, for you to have another breakthrough. Because from what I’ve heard and read, it seems to me that you just try to accomplish the same thing you did with Fear and Loathing in Las Vegas again and again instead of challenging yourself to have a fresh burst of creativity.” He got very angry with me. I said, “I just put it out there because you’re in a new environment. Cuba is so unaffected by Western pop culture that it really gives artists a great, new perspective. It has so much life and spirit, and everybody’s creating and functioning in such an old-fashioned way. I was just suggesting that we take a more laid-back approach.” That really inflamed him. I didn’t want to just write him off as knowing nothing—the guy’s really bright and he’s gotten this far—so I said, “OK. We’ll do it your way. Whatever you want to do.” So we go to sleep. Tomorrow’s another day; we’ll see what happens.

At around four in the morning my phone rang. It was Hunter. “I’ve been trying to call you for three hours! I didn’t realize you had two rooms and I was calling the other room. I really want to talk to you. When I thought about it, you made a lot of sense, and I want to apologize for ripping into you.” I said, “Hey, don’t worry about it. Truthfully, it really didn’t mean that much to me, but let’s just see what happens on its own.”

The first day we had a meeting with some people I know down there who are very heavily involved in the art scene. They were the people I wanted Hunter to meet first so that we set the wheels in motion to have access to other people. In the course of that meeting a friend of Hunter’s who was living on a boat at the marina showed up. We ended up spending the evening with him. He was up to some strange stuff. Once we joined him a flag went up with the Cuban authorities. While he was driving us around we got stopped by the police a couple of times and had to show our IDs, which I had never encountered in all the trips I’d made down there. I thought, “This isn’t a good sign.” This guy, Hunter’s friend, was talking about some sketchy stuff. He had a new Z28 convertible, he had a Honda motorcycle, and he had a boat. It wasn’t clear why he was there, but he wasn’t up to anything good. I said to Hunter, “It’s up to you if this is how you want to spend your time here, but it’s not gonna serve you well.” When we finally left him, Hunter said to me, “Yeah, that guy creeped me out.”

The next day we went for a meeting at an artists’ union where they wanted to introduce Hunter to a bunch of celebrated Cuban writers. During the meeting he was in complete, total Hunter S. Thompson form—funny and weird, but it went right past the Cubans. They weren’t amused by any of it, which was a little scary. It didn’t matter that he was in a strange place where people weren’t really on to his style or his humor; he was going to be himself no matter if people liked him or not.

Hunter S. Thompson in Cuba

The writers’ meeting was hard on everybody, including Hunter. It didn’t seem like he was happy or that things were going well. He really wanted a meeting with Castro. My response was, “Do you think you could just get a meeting with Clinton? Where do you think we are?” By then we’d already blown our first meetings and I wasn’t really getting through to the people who had been accessible to me in the past. There was the first, usual vibe, and then the vibe changed. All of a sudden I felt like, “Wow, I’m really on a different trip this time. Hunter’s not on my trip—I’m on his trip.” Everything was grinding to a halt. I think the pain of having to move around so much also started to overwhelm him. He was scheduled for a double hip replacement when he got back to the US, and Cuba’s such a different environment; it can be taxing to get around and process what’s going on.

I do think that Hunter was on to something in Cuba. We were close, but who knows how close we were to what was going on there politically. There was a story there, but neither side—Cuban nor American—wanted to play along. So we ended up sitting in a Havana hotel room. And maybe that was just Hunter’s fate in Cuba. Or maybe there was nothing to be exposed. Maybe it was all just imaginary. Who knows? I don’t know what he saw from his perspective. He certainly never made it clear to me.

From there we made stuff up. We went to the US Interest Section. The guy who ran it invited us to his house. We had a good time visiting with him. He had an amazing mojito recipe. And then we went back to the marina to visit a bunch of Americans who were in Cuba on a big fishing boat. Hunter knew these guys from the States, so that was a fun evening, but it was not very challenging for him. And he could tell that we weren’t really getting anywhere. He was trying to squeeze whatever he could out of every situation, but in the end there was nothing fulfilled, nothing substantial enough to file. Plus we weren’t filing every day, so there was a constant pressure building.

Hunter S. Thompson and Johnny Depp in Cuba

That’s around the time Johnny joined us. I think he and Hunter became really close during the filming of Fear and Loathing in Las Vegas. From the moment they got together in Cuba they shared this shorthand that I didn’t understand. Johnny was with us for two or three days. In that time I showed him around during the day and then we hung out with Hunter at night. When we were out in the street Johnny wore sunglasses and a Panama hat and had a video camera. I think a few Cubans recognized him, but they didn’t bother him that much. He was just like any other tourist—a tourist who looked a little like Johnny Depp.

He was with us just for a weekend, on a break from filming, and then he left. We had a few days left in Cuba, but I think Hunter was still really struggling with his hips. He wasn’t getting up until the late afternoon, and he wasn’t in the mood to do too much sightseeing. At that point, our interaction with Cuba was limited to going out for meals.

Since the beginning of the trip I had been saying to Hunter that I wanted to collaborate with him on postcards to send to all my friends back in the States. It was the day before we were scheduled to leave and I figured, “I better just do this.” I bought 20 postcards and I went up to his room where he was sitting in his bathrobe reading the newspaper. I said, “I got these postcards. We’re gonna do this thing.” He grumbled, “Bah.” I wrote the first one and tossed it over to him.

I started some of the postcards with, “Dear So and So, Thank you for supporting the Revolution,” and then some crazy personal message. Hunter was really jazzed on that. He started kicking in and writing extra bits, followed by “HST.” All of the sudden it was, “Give me another one…Give me another one…Give me another one.” We went through all 20 of them and then he said, “Go get me 20 more.” So I went down to the lobby and I bought him a whole bunch of postcards.

And then we split. Everything was smooth—we got back to Mexico, we said goodbye. I went to Cabo to surf and start working on my next project.

A couple of days passed and I got this call in my hotel room down in Mexico. To this day I have no idea how he tracked me down. Hunter just had this ability to figure out how to get to somebody, no matter where they were. So he called me in the middle of the night and said, “I have this idea. I think you should come to Colorado and write this article with me. We should collaborate.” I told him, “I’m onto the next adventure now. And anyway, I don’t even know what we could make of it.” There was something about being in Cuba that kept us on level ground. I felt that if I went to Colorado I’d be on his home turf and subject to more of his crazy behavior than I was comfortable with. Besides, I was working on a project down in Mexico at that time, and that was heaven for me. Then he said, “You know, that little session of us writing those postcards together was the most creative I’ve felt in a long time.” All I could tell him was, “Well, then we did it.”

Looking back, I think about how he wrote Fear and Loathing in Las Vegas holed up in a motel room. He was so confined and reduced to so little when I walked in with those postcards.

Maybe there was just this moment of, “No threat, no challenge, no pressure…just write,” that he tapped. Before that he was overthinking. He’d almost become paralyzed by how big he’d gotten.

Hunter went on to write Kingdom of Fear, in which he includes a section on his trip to Cuba. He describes me as, “a swarthy little man wearing a seersucker coat and a goofy grin of a surfer” who “introduced himself as a famous rock and roll photographer.” It was an honor just to be mentioned.